This study examines the course of Greek–Serbian relations in the late 19th and early 20th centuries, when the main concern of both sides was the division of Ottoman Macedonia into spheres of influence. The author deepens the research by highlighting the factors that played a decisive role in the evolution of the negotiations, the perspective of each side regarding the nature and prospects of the planned Greek–Serbian rapprochement, as well as the priorities and objectives of the two countries. At the same time, the study explores specific issues such as the Serbian perspective on the question of a Balkan Federation, the different aspects of Serbian policy concerning the autonomy of Macedonia, and finally attempts an overview of Greek–Serbian relations during the period of the Macedonian Struggle.